Lithium Hydroxide → HCID 21830433, compound

HRID 1601079Notes

Reaction equation

HRID 1601079 reaction equation
[Li+].[OH-].[N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5][C:4]=1[CH2:12][NH:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]2[NH:24][CH:23]([CH2:25][C:26]([O:28]C)=[O:27])[C:22](=[O:30])[N:21]([CH3:31])[CH2:20][C:19]=2[CH:32]=1>O1CCOCC1.O>[N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5][C:4]=1[CH2:12][NH:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]2[NH:24][CH:23]([CH2:25][C:26]([OH:28])=[O:27])[C:22](=[O:30])[N:21]([CH3:31])[CH2:20][C:19]=2[CH:32]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 54527618HCID 54527618, compound

Product 1

HCID 21830433HCID 21830433, compoundYield 53.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

LiOH (14.6 mg, 0.34 mmol) was added at RT to a solution of methyl (±)-7-[[[(2-benzimidazolyl)methyl]amino]methyl]-4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2-acetate (133 mg, 0.31 mmol) in dioxane (3 mL) and H2O (1 mL). The reaction mixture was stirred at RT overnight then the organic solvent was removed in vacuo. The aqueous residue was acidified with 1M HCl solution (0.38 mL) to obtain a white solid which was purified by ODS chromatography (10% acetonitrile/H2O-0.1% TFA) to afford the title compound (65 mg, 51%): 1H NMR (DMSO-d6, 400 MHz) δ 2.51 (m, 1H), 2.73 (m, 1H), 2.91 (s, 3H), 3.69 (bs, 2H), 3.76 (d, J=16.6 Hz, 1H), 3.97 (br s, 2H), 4.97 (m, 1H), 4.45 (d, J=16.6 Hz, 1H), 5.77 (m, 1H), 6.52 (d, J=8.1 Hz, 1H), 6.97 (s, 1H), 7.02 (d, J=8.1 Hz, 1H), 7.20 (m, 2H), 7.52 (m, 2H); MS (ES) m/e 394 (M+H)+. Anal. Calcd. for C21H23N5O3.2 CF3CO2H.H2O: C, 46.95; H, 4.26; N, 10.95. Found: C, 46.81; H, 4.00; N, 10.84.

Workup

  1. customthe organic solvent was removed in vacuo
  2. customto obtain a white solid which
  3. customwas purified by ODS chromatography (10% acetonitrile/H2O-0.1% TFA)

Sources & evidence

ORD record
ord-cd81bd36c6154be5a871df12e716c386
Source dataset
uspto-grants-1999_11
Patent number
US05977101

Reaction notes

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